2-[1-(4-Ethoxy­phen­yl)-2-oxo-4-styryl­azetidin-3-yl]isoindoline-1,3-dione

Akkurt, M.; Karaca, S.; Jarrahpour, A.A.; Zarei, M.; Büyükgüngör, O.

doi:10.1107/S1600536808011586

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o924

doi:10.1107/S1600536808011586

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2-[1-(4-Ethoxyphenyl)-2-oxo-4-styrylazetidin-3-yl]isoindoline-1,3-dione

Mehmet Akkurt,^a ^* Selvi Karaca,^a Ali Asghar Jarrahpour,^b Maaroof Zarei ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 4 April 2008; accepted 22 April 2008; online 26 April 2008)

The title compound, C₂₇H₂₂N₂O₄, contains a nearly planar four-membered β-lactam ring, which makes dihedral angles of 74.64 (12), 1.70 (11) and 73.67 (12)° with the nine-membered ring system, the benzene ring and the phenyl ring, respectively. The crystal structure is stabilized by C—H⋯O and C—H⋯π interactions and a π–π interaction [centroid–centroid distance = 3.4505 (19) Å] is also present.

Related literature

For related structures, see: Pınar et al. (2006 ); Akkurt et al. (2007 ). For background, see: Halve et al. (2007 ); Aoyama et al. (2001 ). For related literature, see: Jarrahpour & Zarei (2007 ).

Experimental

Crystal data

C₂₇H₂₂N₂O₄
M_r = 438.47
Monoclinic, C 2/c
a = 33.7560 (17) Å
b = 7.0403 (2) Å
c = 31.0482 (17) Å
β = 140.454 (3)°
V = 4698.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.53 × 0.45 × 0.14 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: none
22562 measured reflections
4934 independent reflections
3071 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.099
S = 0.96
4934 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.93	2.53	3.283 (3)	138
C5—H5⋯O3ⁱⁱ	0.93	2.47	3.257 (3)	142
C13—H13⋯O3	0.93	2.53	3.139 (2)	123
C20—H20⋯O2ⁱⁱⁱ	0.93	2.51	3.374 (2)	156
C9—H9⋯Cg1^iv	0.98	2.84	3.7938 (16)	166
C19—H19C⋯Cg2^v	0.96	2.82	3.633 (4)	143
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+1; (iii) x, y-1, z; (iv) x, y+1, z; (v) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ . Cg1 is the centroid of atoms C12–C17 and Cg2 is the centroid of atoms C2–C7.

Data collection: X-AREA (Stoe & Cie, 2002 ); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011586/hb2715sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011586/hb2715Isup2.hkl

checkCIF report

Comment top

The 2-azetidinone ring system is the common structural feature of a number of broad spectrum β-lactam antibiotics (Halve et al., 2007) and also possesses other pharmalogical properties (Aoyama et al., 2001). As part of our onging studies of such materials (Pınar et al., 2006; Akkurt et al., 2007), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

The four-membered β-lactam ring in (I) is nearly planar, with maximum deviations of 0.022 (1) Å for N2 and -0.021 (2) Å for C10. Within the lactam ring, the bond lengths are similar to those observed in our previous studies (Pınar et al., 2006; Akkurt et al., 2007).

The four-membered β-lactam ring (N2/C9–C11) in (I) makes dihedral angles of 74.64 (12), 1.70 (11) and 73.67 (12)° with the nine-membered ring system (A: N1/C1–C8) {max. deviations from planarity = 0.048 (2) for N1 and -0.029 (3) Å for C2 and C7}, the benzene ring (B: C12–C17) and the phenyl ring (C: C22–C27), respectively. The other dihedral angles are A/B = 74.74 (9), A/C = 55.97 (11) and B/C = 74.84 (10)°. The sum of the bond angles about atom N2 is 360.0°.

The packing and hydrogen bonding of the title compound is shown in Fig. 2. The crystal structure is stabilized by inter- and intramolecular C—H···O interactions and C—H···π contacts (Table 1). Finally, an aromatic π—π stacking interaction {C_g3···C_g2(1 – x, 2 – y,1 – z) = 3.4505 (19)Å, where C_g3 is the centroid of the N1/C1/C2/C7/C8 five-membered ring} is observed in the crystal structure.

Related literature top

For related structures, see: Pınar et al. (2006); Akkurt et al. (2007). For background, see: Halve et al. (2007); Aoyama et al. (2001). For related literature, see: Jarrahpour & Zarei (2007).

Experimental top

A solution of Schiff base (4-cinnamylidene)-(4-ethoxyphenyl)amine (1.0 eq.) was stirred with Phthaloylglycine (1.5 eq.), p-toluenesulfonyl chloride (1.5 eq.) and triethylamine (5 eq.) in dry CH₂Cl₂ at room temperature. After 10 h, the mixture was washed with saturated sodium bicarbonate solution and brine, dried over sodium sulfate and the solvent was evaporated to give the crude product which was then purified by recrystalization from EtOAc (Jarrahpour & Zarei, 2007) [mp: 434 -436 K]. IR (CHCl₃) cm^-1: 1724.2, 1758.5 (CO, phth), 1774.7 (CO, β-lactam); ¹H NMR (250 MHz, CDCl₃) δ 1.37 (Me, t, 3H), 2.33 (Me, s, 3H), 3.97 (OCH₂, q, 2H), 5.03 (H-4, dd, 1H, J=5.5, 8.5), 5.68 (H-3, d, 1H, J=5.5), 6.32 (H-5, dd, J=8.5, 16.0), 6.85 (H-6, d, 1H, J=9.0), 7.19-7.82 (ArH, m, 13H); ¹³C NMR (62.9 MHz, CDCl₃) δ 14.78 (Me), 57.69 (OCH₂), 61.04 (C-4), 63.67 (C-3), 114.99-155.82 (C=C, aromatic carbons), 160.56 (CO, phth), 167.28 (CO, β-lactam); GC-MS m/z = 438 [M⁺]. Analysis calculated for C₂₇H₂₂N₂O₄: C 73.96, H 5.06, N 6.39%. Found: C 74.02, H 5.09, N 6.33%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the molecular structure of (I), with 30% probability displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. View of the packing and hydrogen bonding interactions for (I). H atoms not involved in hydrogen bonding have been omitted for clarity.

2-[1-(4-Ethoxyphenyl)-2-oxo-4-styrylazetidin-3-yl]isoindoline-1,3-dione top

Crystal data top

C₂₇H₂₂N₂O₄	F(000) = 1840
M_r = 438.47	D_x = 1.240 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 19454 reflections
a = 33.7560 (17) Å	θ = 1.3–27.3°
b = 7.0403 (2) Å	µ = 0.08 mm⁻¹
c = 31.0482 (17) Å	T = 293 K
β = 140.454 (3)°	Prism, colourless
V = 4698.0 (5) Å³	0.53 × 0.45 × 0.14 mm
Z = 8

Data collection top

Stoe IPDS-2 diffractometer	3071 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	R_int = 0.052
Plane graphite monochromator	θ_max = 26.8°, θ_min = 1.4°
Detector resolution: 6.67 pixels mm^-1	h = −42→42
ω scans	k = −8→8
22562 measured reflections	l = −39→39
4934 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
4934 reflections	Δρ_max = 0.17 e Å⁻³
299 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (2)

Crystal data top

C₂₇H₂₂N₂O₄	V = 4698.0 (5) Å³
M_r = 438.47	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 33.7560 (17) Å	µ = 0.08 mm⁻¹
b = 7.0403 (2) Å	T = 293 K
c = 31.0482 (17) Å	0.53 × 0.45 × 0.14 mm
β = 140.454 (3)°

Data collection top

Stoe IPDS-2 diffractometer	3071 reflections with I > 2σ(I)
22562 measured reflections	R_int = 0.052
4934 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 0.97	Δρ_max = 0.17 e Å⁻³
4934 reflections	Δρ_min = −0.11 e Å⁻³
299 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.52753 (6)	0.55052 (15)	0.57556 (7)	0.0765 (5)
O2	0.54065 (6)	1.14698 (16)	0.64241 (7)	0.0887 (5)
O3	0.67821 (7)	0.6142 (2)	0.70712 (8)	0.1034 (6)
O4	0.74347 (5)	−0.13874 (15)	0.89253 (6)	0.0729 (4)
N1	0.54930 (5)	0.83949 (16)	0.62525 (6)	0.0555 (4)
N2	0.64313 (6)	0.53412 (18)	0.74672 (7)	0.0617 (4)
C1	0.51510 (7)	0.7165 (2)	0.57070 (8)	0.0562 (5)
C2	0.46331 (7)	0.8305 (2)	0.50943 (8)	0.0554 (5)
C3	0.41750 (8)	0.7826 (3)	0.44180 (9)	0.0708 (6)
C4	0.37641 (8)	0.9267 (3)	0.39554 (10)	0.0814 (8)
C5	0.38151 (9)	1.1085 (3)	0.41602 (11)	0.0795 (8)
C6	0.42714 (8)	1.1549 (2)	0.48327 (10)	0.0714 (7)
C7	0.46791 (7)	1.0133 (2)	0.52986 (8)	0.0566 (5)
C8	0.52172 (7)	1.0197 (2)	0.60414 (9)	0.0598 (5)
C9	0.60433 (7)	0.7905 (2)	0.69508 (8)	0.0641 (5)
C10	0.64799 (8)	0.6362 (3)	0.71402 (9)	0.0719 (6)
C11	0.59771 (7)	0.6599 (2)	0.72999 (8)	0.0597 (5)
C12	0.67075 (7)	0.3647 (2)	0.78458 (8)	0.0567 (5)
C13	0.71296 (7)	0.2662 (2)	0.79469 (8)	0.0597 (5)
C14	0.73897 (7)	0.0980 (2)	0.83145 (8)	0.0601 (5)
C15	0.72250 (7)	0.0284 (2)	0.85749 (8)	0.0580 (5)
C16	0.68038 (7)	0.1281 (2)	0.84731 (9)	0.0639 (6)
C17	0.65484 (7)	0.2938 (2)	0.81140 (8)	0.0640 (6)
C18	0.79389 (8)	−0.2335 (3)	0.91444 (10)	0.0753 (7)
C19	0.81168 (9)	−0.3978 (3)	0.95687 (10)	0.0799 (7)
C20	0.53523 (7)	0.5771 (2)	0.68565 (8)	0.0564 (5)
C21	0.49520 (7)	0.6482 (2)	0.67920 (9)	0.0672 (6)
C22	0.43110 (8)	0.5844 (2)	0.63340 (9)	0.0655 (6)
C23	0.40642 (9)	0.4242 (3)	0.59366 (12)	0.0936 (8)
C24	0.34510 (11)	0.3722 (3)	0.54989 (13)	0.1084 (10)
C25	0.30869 (9)	0.4779 (3)	0.54607 (12)	0.0919 (8)
C26	0.33206 (9)	0.6339 (3)	0.58488 (10)	0.0815 (7)
C27	0.39250 (8)	0.6879 (3)	0.62798 (9)	0.0726 (6)
H3	0.41420	0.66050	0.42780	0.0850*
H4	0.34460	0.89950	0.34950	0.0980*
H5	0.35350	1.20120	0.38360	0.0950*
H6	0.43060	1.27740	0.49710	0.0860*
H9	0.62800	0.90510	0.72220	0.0770*
H11	0.61500	0.71940	0.77040	0.0720*
H13	0.72390	0.31270	0.77680	0.0720*
H14	0.76750	0.03250	0.83850	0.0720*
H16	0.66940	0.08180	0.86510	0.0770*
H17	0.62660	0.35940	0.80490	0.0770*
H18A	0.82890	−0.14760	0.94060	0.0900*
H18B	0.78150	−0.27720	0.87570	0.0900*
H19A	0.77670	−0.48160	0.93060	0.0960*
H19B	0.82430	−0.35290	0.99530	0.0960*
H19C	0.84560	−0.46500	0.97210	0.0960*
H20	0.52400	0.46840	0.66110	0.0680*
H21	0.50880	0.75120	0.70680	0.0810*
H23	0.43100	0.35050	0.59620	0.1120*
H24	0.32880	0.26450	0.52300	0.1300*
H25	0.26760	0.44230	0.51660	0.1100*
H26	0.30720	0.70510	0.58250	0.0980*
H27	0.40790	0.79670	0.65410	0.0870*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0929 (9)	0.0524 (6)	0.0847 (9)	0.0128 (6)	0.0686 (8)	0.0056 (6)
O2	0.0932 (9)	0.0554 (6)	0.0838 (9)	0.0000 (6)	0.0594 (8)	−0.0081 (7)
O3	0.0824 (9)	0.1325 (11)	0.1212 (12)	0.0437 (8)	0.0853 (10)	0.0642 (9)
O4	0.0679 (7)	0.0707 (7)	0.0925 (9)	0.0208 (6)	0.0651 (7)	0.0242 (6)
N1	0.0501 (7)	0.0471 (6)	0.0569 (8)	0.0026 (5)	0.0380 (7)	0.0046 (6)
N2	0.0499 (7)	0.0691 (8)	0.0602 (8)	0.0122 (6)	0.0409 (7)	0.0166 (7)
C1	0.0574 (9)	0.0528 (8)	0.0646 (10)	0.0019 (7)	0.0487 (9)	0.0029 (8)
C2	0.0488 (8)	0.0622 (9)	0.0601 (10)	0.0012 (7)	0.0433 (8)	0.0039 (8)
C3	0.0620 (10)	0.0890 (11)	0.0675 (12)	−0.0043 (9)	0.0515 (10)	−0.0026 (10)
C4	0.0527 (10)	0.1283 (17)	0.0578 (11)	0.0072 (11)	0.0412 (10)	0.0174 (11)
C5	0.0597 (11)	0.0968 (14)	0.0827 (15)	0.0211 (10)	0.0551 (12)	0.0319 (11)
C6	0.0641 (10)	0.0658 (10)	0.0866 (14)	0.0161 (8)	0.0587 (11)	0.0234 (9)
C7	0.0491 (8)	0.0547 (8)	0.0671 (10)	0.0053 (7)	0.0451 (9)	0.0103 (7)
C8	0.0593 (9)	0.0477 (8)	0.0698 (11)	−0.0010 (7)	0.0491 (10)	0.0023 (8)
C9	0.0488 (8)	0.0616 (9)	0.0589 (10)	−0.0025 (7)	0.0355 (8)	0.0039 (8)
C10	0.0504 (9)	0.0870 (12)	0.0687 (11)	0.0113 (8)	0.0434 (9)	0.0225 (9)
C11	0.0522 (8)	0.0608 (8)	0.0548 (9)	0.0044 (7)	0.0383 (8)	0.0025 (7)
C12	0.0421 (7)	0.0642 (9)	0.0496 (9)	0.0026 (7)	0.0316 (7)	0.0061 (7)
C13	0.0462 (8)	0.0729 (9)	0.0568 (9)	0.0006 (7)	0.0389 (8)	0.0050 (8)
C14	0.0456 (8)	0.0676 (9)	0.0649 (10)	0.0045 (7)	0.0420 (8)	0.0050 (8)
C15	0.0477 (8)	0.0627 (9)	0.0574 (10)	0.0050 (7)	0.0389 (8)	0.0057 (7)
C16	0.0607 (9)	0.0717 (10)	0.0670 (11)	0.0111 (8)	0.0513 (9)	0.0141 (8)
C17	0.0562 (9)	0.0744 (10)	0.0639 (10)	0.0152 (8)	0.0470 (9)	0.0130 (8)
C18	0.0659 (10)	0.0775 (11)	0.0890 (13)	0.0206 (9)	0.0614 (11)	0.0174 (10)
C19	0.0763 (12)	0.0824 (11)	0.0857 (13)	0.0266 (9)	0.0637 (12)	0.0206 (10)
C20	0.0555 (9)	0.0539 (8)	0.0560 (9)	0.0039 (7)	0.0420 (8)	0.0030 (7)
C21	0.0574 (9)	0.0721 (10)	0.0643 (11)	−0.0014 (8)	0.0449 (9)	−0.0129 (8)
C22	0.0579 (9)	0.0755 (10)	0.0638 (10)	−0.0002 (8)	0.0471 (9)	−0.0060 (8)
C23	0.0762 (13)	0.0912 (13)	0.1146 (17)	−0.0156 (10)	0.0739 (14)	−0.0352 (12)
C24	0.0876 (15)	0.1084 (16)	0.124 (2)	−0.0347 (13)	0.0802 (16)	−0.0474 (14)
C25	0.0647 (11)	0.1170 (16)	0.0931 (15)	−0.0159 (12)	0.0606 (12)	−0.0111 (13)
C26	0.0662 (11)	0.1067 (14)	0.0831 (13)	0.0048 (11)	0.0606 (11)	0.0017 (12)
C27	0.0659 (11)	0.0863 (11)	0.0715 (11)	0.0024 (9)	0.0545 (10)	−0.0063 (9)

Geometric parameters (Å, º) top

O1—C1	1.211 (2)	C21—C22	1.470 (4)
O2—C8	1.205 (2)	C22—C23	1.380 (3)
O3—C10	1.203 (5)	C22—C27	1.385 (4)
O4—C15	1.3717 (18)	C23—C24	1.388 (5)
O4—C18	1.421 (4)	C24—C25	1.362 (6)
N1—C1	1.3913 (19)	C25—C26	1.347 (3)
N1—C8	1.402 (2)	C26—C27	1.374 (4)
N1—C9	1.435 (2)	C3—H3	0.9300
N2—C10	1.353 (3)	C4—H4	0.9300
N2—C11	1.475 (3)	C5—H5	0.9300
N2—C12	1.408 (2)	C6—H6	0.9300
C1—C2	1.480 (2)	C9—H9	0.9800
C2—C3	1.381 (2)	C11—H11	0.9800
C2—C7	1.390 (2)	C13—H13	0.9300
C3—C4	1.394 (3)	C14—H14	0.9300
C4—C5	1.380 (3)	C16—H16	0.9300
C5—C6	1.371 (3)	C17—H17	0.9300
C6—C7	1.382 (2)	C18—H18A	0.9700
C7—C8	1.470 (2)	C18—H18B	0.9700
C9—C10	1.537 (4)	C19—H19A	0.9600
C9—C11	1.563 (3)	C19—H19B	0.9600
C11—C20	1.485 (3)	C19—H19C	0.9600
C12—C13	1.386 (4)	C20—H20	0.9300
C12—C17	1.386 (4)	C21—H21	0.9300
C13—C14	1.389 (2)	C23—H23	0.9300
C14—C15	1.377 (4)	C24—H24	0.9300
C15—C16	1.386 (4)	C25—H25	0.9300
C16—C17	1.366 (2)	C26—H26	0.9300
C18—C19	1.488 (3)	C27—H27	0.9300
C20—C21	1.304 (4)

C15—O4—C18	118.5 (2)	C24—C25—C26	120.1 (3)
C1—N1—C8	111.45 (13)	C25—C26—C27	120.2 (3)
C1—N1—C9	125.59 (13)	C22—C27—C26	121.6 (2)
C8—N1—C9	122.91 (13)	C2—C3—H3	122.00
C10—N2—C11	96.40 (17)	C4—C3—H3	122.00
C10—N2—C12	133.7 (3)	C3—C4—H4	119.00
C11—N2—C12	129.9 (2)	C5—C4—H4	119.00
O1—C1—N1	124.49 (15)	C4—C5—H5	119.00
O1—C1—C2	129.48 (15)	C6—C5—H5	119.00
N1—C1—C2	106.03 (13)	C5—C6—H6	121.00
C1—C2—C3	130.54 (16)	C7—C6—H6	121.00
C1—C2—C7	108.06 (14)	N1—C9—H9	110.00
C3—C2—C7	121.35 (16)	C10—C9—H9	110.00
C2—C3—C4	116.54 (19)	C11—C9—H9	110.00
C3—C4—C5	121.93 (19)	N2—C11—H11	112.00
C4—C5—C6	121.16 (19)	C9—C11—H11	112.00
C5—C6—C7	117.70 (16)	C20—C11—H11	112.00
C2—C7—C6	121.31 (15)	C12—C13—H13	120.00
C2—C7—C8	108.22 (14)	C14—C13—H13	120.00
C6—C7—C8	130.44 (15)	C13—C14—H14	120.00
O2—C8—N1	123.78 (16)	C15—C14—H14	120.00
O2—C8—C7	130.10 (16)	C15—C16—H16	120.00
N1—C8—C7	106.12 (13)	C17—C16—H16	120.00
N1—C9—C10	119.36 (17)	C12—C17—H17	120.00
N1—C9—C11	118.6 (2)	C16—C17—H17	120.00
C10—C9—C11	85.79 (16)	O4—C18—H18A	110.00
O3—C10—N2	132.5 (2)	O4—C18—H18B	110.00
O3—C10—C9	135.9 (2)	C19—C18—H18A	110.00
N2—C10—C9	91.6 (2)	C19—C18—H18B	110.00
N2—C11—C9	86.09 (19)	H18A—C18—H18B	109.00
N2—C11—C20	115.99 (14)	C18—C19—H19A	109.00
C9—C11—C20	116.63 (14)	C18—C19—H19B	110.00
N2—C12—C13	121.1 (2)	C18—C19—H19C	109.00
N2—C12—C17	119.5 (2)	H19A—C19—H19B	110.00
C13—C12—C17	119.40 (16)	H19A—C19—H19C	109.00
C12—C13—C14	120.1 (2)	H19B—C19—H19C	109.00
C13—C14—C15	120.0 (2)	C11—C20—H20	118.00
O4—C15—C14	125.2 (2)	C21—C20—H20	118.00
O4—C15—C16	115.3 (2)	C20—C21—H21	116.00
C14—C15—C16	119.57 (16)	C22—C21—H21	116.00
C15—C16—C17	120.6 (3)	C22—C23—H23	120.00
C12—C17—C16	120.3 (3)	C24—C23—H23	120.00
O4—C18—C19	107.8 (3)	C23—C24—H24	120.00
C11—C20—C21	123.68 (16)	C25—C24—H24	120.00
C20—C21—C22	127.56 (17)	C24—C25—H25	120.00
C21—C22—C23	122.6 (3)	C26—C25—H25	120.00
C21—C22—C27	120.12 (16)	C25—C26—H26	120.00
C23—C22—C27	117.3 (3)	C27—C26—H26	120.00
C22—C23—C24	120.5 (3)	C22—C27—H27	119.00
C23—C24—C25	120.4 (2)	C26—C27—H27	119.00

C18—O4—C15—C16	−170.02 (15)	C4—C5—C6—C7	0.1 (5)
C18—O4—C15—C14	11.6 (2)	C5—C6—C7—C8	178.3 (3)
C15—O4—C18—C19	174.18 (14)	C5—C6—C7—C2	0.6 (5)
C9—N1—C1—C2	−179.5 (2)	C6—C7—C8—N1	−175.1 (3)
C9—N1—C1—O1	0.5 (5)	C2—C7—C8—N1	2.8 (3)
C1—N1—C9—C10	30.8 (4)	C6—C7—C8—O2	5.8 (6)
C8—N1—C9—C10	−152.3 (2)	C2—C7—C8—O2	−176.3 (3)
C8—N1—C1—C2	3.2 (3)	C10—C9—C11—C20	−114.35 (19)
C1—N1—C8—O2	175.4 (3)	N1—C9—C10—O3	60.1 (3)
C9—N1—C8—O2	−1.9 (5)	N1—C9—C11—C20	7.0 (3)
C1—N1—C8—C7	−3.8 (3)	C11—C9—C10—O3	−179.3 (2)
C9—N1—C8—C7	178.9 (2)	N1—C9—C11—N2	124.16 (17)
C8—N1—C1—O1	−176.8 (3)	C10—C9—C11—N2	2.85 (12)
C8—N1—C9—C11	105.6 (2)	N1—C9—C10—N2	−123.7 (2)
C1—N1—C9—C11	−71.3 (3)	C11—C9—C10—N2	−3.10 (13)
C10—N2—C12—C17	−179.02 (18)	C9—C11—C20—C21	−98.1 (3)
C11—N2—C12—C17	0.9 (3)	N2—C11—C20—C21	162.74 (18)
C12—N2—C11—C9	176.79 (16)	C13—C12—C17—C16	−0.2 (2)
C10—N2—C12—C13	0.1 (3)	N2—C12—C13—C14	−179.13 (15)
C11—N2—C12—C13	−179.98 (15)	N2—C12—C17—C16	178.93 (15)
C12—N2—C10—O3	−0.4 (4)	C17—C12—C13—C14	0.0 (2)
C12—N2—C11—C20	−65.4 (2)	C12—C13—C14—C15	0.4 (2)
C10—N2—C11—C20	114.56 (19)	C13—C14—C15—C16	−0.6 (2)
C10—N2—C11—C9	−3.25 (13)	C13—C14—C15—O4	177.73 (15)
C11—N2—C10—O3	179.7 (2)	C14—C15—C16—C17	0.4 (3)
C11—N2—C10—C9	3.30 (14)	O4—C15—C16—C17	−178.09 (15)
C12—N2—C10—C9	−176.74 (17)	C15—C16—C17—C12	0.0 (3)
N1—C1—C2—C7	−1.4 (3)	C11—C20—C21—C22	175.49 (18)
N1—C1—C2—C3	176.2 (3)	C20—C21—C22—C23	5.4 (3)
O1—C1—C2—C7	178.6 (3)	C20—C21—C22—C27	−173.5 (2)
O1—C1—C2—C3	−3.8 (6)	C21—C22—C23—C24	−178.4 (2)
C3—C2—C7—C6	−0.6 (5)	C27—C22—C23—C24	0.6 (4)
C1—C2—C3—C4	−177.3 (3)	C21—C22—C27—C26	179.0 (2)
C7—C2—C3—C4	−0.1 (5)	C23—C22—C27—C26	0.0 (3)
C3—C2—C7—C8	−178.7 (3)	C22—C23—C24—C25	−0.6 (4)
C1—C2—C7—C8	−0.9 (3)	C23—C24—C25—C26	0.0 (4)
C1—C2—C7—C6	177.2 (3)	C24—C25—C26—C27	0.6 (4)
C2—C3—C4—C5	0.7 (5)	C25—C26—C27—C22	−0.6 (4)
C3—C4—C5—C6	−0.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.53	3.283 (3)	138
C5—H5···O3ⁱⁱ	0.93	2.47	3.257 (3)	142
C13—H13···O3	0.93	2.53	3.139 (2)	123
C20—H20···O2ⁱⁱⁱ	0.93	2.51	3.374 (2)	156
C9—H9···C_g1^iv	0.98	2.84	3.7938 (16)	166
C19—H19C···C_g2^v	0.96	2.82	3.633 (4)	143

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, y−1, z; (iv) x, y+1, z; (v) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₂N₂O₄
M_r	438.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	33.7560 (17), 7.0403 (2), 31.0482 (17)
β (°)	140.454 (3)
V (Å³)	4698.0 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.53 × 0.45 × 0.14

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22562, 4934, 3071
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.099, 0.97
No. of reflections	4934
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.11

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.53	3.283 (3)	138
C5—H5···O3ⁱⁱ	0.93	2.47	3.257 (3)	142
C13—H13···O3	0.93	2.53	3.139 (2)	123
C20—H20···O2ⁱⁱⁱ	0.93	2.51	3.374 (2)	156
C9—H9···C_g1^iv	0.98	2.84	3.7938 (16)	166
C19—H19C···C_g2^v	0.96	2.82	3.633 (4)	143

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, y−1, z; (iv) x, y+1, z; (v) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

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